If the Director of Retail is the head coach and the Head of Operations is the offensive coordinator, then the VP of Stores is the general manager. He is one who sets the vision, controls the budget, and has to sit in front of the C-Suite every Monday morning with a deck of KPIs. In other words: when the holidays roll around, the VP of Stores isn’t just managing chaos, he’s the one orchestrating it into measurable, and hopefully reportable ROI.

For high-growth brands with big omnichannel ambitions, the holiday season is where strategy either shines like a Rockefeller Center tree… or fizzles out faster than that cheap string of lights you bought last year. The VP of Stores has to align the in-store experience with the digital brand, prove that outreach drives revenue, and launch loyalty programs that don’t just sound fancy but actually deliver repeat sales.

So how does the VP of Stores pull off a holiday season worthy of a standing ovation in the boardroom? Let’s unwrap some strategies.

Today’s shoppers, especially luxury shoppers, expect consistency from the digital to the physical (and vice versa). They don’t want to feel like they’re stepping from the grandiosity of Home Alone to a lackluster Home Alone 3. The vibe online has to match the vibe in-store.

In order to do that this holiday season, the VP of Stores should keep a few points in mind, including:

• Unified data: Store associates should know what a customer browsed online when they walk in.
• Visual cohesion: If your ecommerce site is hyping the “Holiday Drop,” your stores need the same look and feel across your signage, playlists, and even scents.
• Consistent messaging: A VIP email offering early access to a collection should match what your associates are saying on the sales floor.
  

The VP of Stores can make this alignment a reality by investing in a solid retail CRM that integrates directly with Shopify and all of your marketing tools. No custom dev. No swivel-chairing between dashboards. No sifting through a hundred different Excel spreadsheets and data sources. Just a single source of truth right there in your CRM, which acts as your command center.

It’s 2025. We all know (or should know) that ad hoc holiday outreach just doesn’t cut it anymore in this era of truly personalized, clienteling retail. Associates randomly texting clients solely from their personal phones? That’s like Santa keeping his naughty/nice database on sticky notes.

The VP of Stores needs repeatable, measurable outreach programs that can scale across dozens of associates and multiple stores. These days, customer data drives outreach campaigns that achieve ROI, not just gut feelings. For your store teams to have these types of effective programs, the VP has to think more technically and methodically with:

• Standardized templates for gifting, new arrivals, and loyalty invites.
• Automated segmentation so VIPs get special treatment and first-timers get warm introductions, all without manual sorting.
• Appointment flows that follow a clear timeline: invite, confirm, follow-up, convert.
  

The beauty is that once these programs are in place, they’re not just for the holidays. They can be reused (and refined) year-round. And of course, they’re finally measurable enough to defend budget requests to the CFO.

Speaking of which…

The holiday season is where the VP of Stores earns their stripes, especially during the gauntlet between Thanksgiving and Cyber Monday where nearly 40% of holiday spend happens. To be informative and accurate, weekly performance updates need to be much more than just, “Traffic seemed good” or “Associates worked really hard.”

The C-Suite wants numbers, and the VP needs tools that make all the clienteling his stores are doing measurable:

• Outreach volume by associate
• Conversion rate from outreach to sale
• Average order value on appointment customers vs. walk-ins
• Loyalty enrollments linked to in-store activity
  

Your retail CRM should provide these types of KPIs at-a-glance because the holidays are simply much too busy to have to sift through raw numbers and do VLOOKUPS on the fly. VPs need dashboards that not only aggregate numbers, but display trends to easily see what’s working and what’s not. So when you can walk into the Monday exec meeting and say, “Our clienteling outreach drove 22% of holiday revenue across stores,” that’s not just a win, that’s a testament to all the hard work from your team.

Many VPs of Stores have lived through failed tech rollouts. Salesforce, enterprise platforms built for B2B sales teams, insert-your-overpriced-tool-here. The problem isn’t what these tools can or cannot do, it’s adoption. A Bugatti is sweet, but if your team can’t be bothered to learn paddle stick shifts while working overtime to cater to holiday VIPs, the most state-of-the-art car is rendered useless.

This holiday season, don’t burden associates with software that requires weeks or months of acclimation and learning. A savvy VP should choose tools that are intuitive, mobile-friendly, and actually help them sell more.

Because at the end of the day, associates aren’t motivated by “system usage rates.” They’re motivated by closing sales and making customers happy. Give them a retail CRM that feels like a superpower, not a chore, and suddenly adoption stops being an issue.

Luxury customers don’t just want transactions. They want access. They want to feel like insiders. Think early access, limited editions, and white-glove-level clienteling. The VP of Stores can take advantage of this by rolling out elevated loyalty and appointment programs just in time for the holidays.

Some ideas:

• Holiday VIP appointments: Invite top customers for private shopping hours, complete with seasonal perks.
• Tiered loyalty perks: Give Platinum members early access to the Holiday Drop before it hits shelves.
• Personal concierge follow-ups: After an appointment, associates send curated lookbooks via text or email, personalized to that customer’s tastes.
  

These programs not only increase sales during December but also set the tone for 2025. The holidays become the launchpad for year-round loyalty.

The best and most productive retail teams don’t just rely on a handful of “rockstar” associates. While there will always be overachievers, it’s always better when every store rep performs like a seasoned pro. Not only does it make for great ROI, but it makes the VP’s life a whole lot easier.

How do you get there? Training. Not just for positive customer interactions, but also on the tools they have access to that can make the floor team much more effective during their busiest hours. Some tips:

• Unified customer profiles: Give every associate the same access to data. That way, even the seasonal hire knows what a repeat customer bought last December. Less scrambling and asking; more clienteling and selling.
• AI-powered assistance: Suggested replies, conversation recaps, and tone adjustments give associates confidence in their outreach.
• Performance tracking: Associates can see their own outreach numbers and results, making the connection between effort and ROI tangible.
  

When everyone has the same playbook and tools, you don’t just have a few holiday heroes. You have an all-star team.

The holidays are prime time for acquisition, but the VP of Stores knows the real game is retention. December is when your stores get into the black, but January is when the brand can turn one-time gifters into loyal customers.

That means giving consideration to the entire customer journey, especially if a brand new shoppers walks in and your team is able to make a great first impression. The VP of Stores should make sure that his team is ready to do the following:

• Scheduling post-holiday follow-ups for every new customer.
• Offering bounce-back incentives (“Come back in January and enjoy 15% off your next look”).
• Tracking repeat purchase rates to see how well holiday shoppers convert to long-term customers in the next few months.
  

Because while December revenue makes the headlines, January loyalty builds the legacy.

For the VP of Stores, the holiday season isn’t just about making the registers sing. It’s about proving that in-store clienteling is a true revenue engine, not just to the team, but to the boardroom. The strategies outlined here can go a long way to help maximize the efforts of a solid sales team.

And of course, a great retail CRM can give you the evidence that stores didn’t just survive the holiday rush, but drove the kind of ROI that makes any C-suite executives’ hearts grow three times in size.